Groupon’s project managers are 'the air traffic controllers of the engineering department'

by Paul Rogers

October 30, 2017

Photographs by Chris Murphy

It was 4 a.m. when confirmation finally came in from the engineers: Groupon had successfully completed the online integration of LivingSocial, which the company acquired in 2016.

Groupon’s project management team had been toiling for months, working with engineers and key stakeholders on this large-scale project. With about 50 other staffers from different departments, they waited and watched into the wee hours, some via conference, until the “cutover” was finally confirmed. This means that users could now access the integrated content — and two weeks ahead of schedule.

That's when an engineer came in with a bottle of Cristal and a “cutover” cannoli cake.

"Besides my wedding cake, that was the best cake I’ve ever had," said Karen Hyatt, technical project manager. "There was something about being bleary-eyed at 4 a.m., eating cutover cake with the team you worked so hard with over six months that was really just special."

Such spirit of togetherness is typical for this close-knit team, known formally as the project management organization.

We recently spoke with the crew to find out how they manage to complete their highly visible work while always being there for each other – and for cake.

THE TEAM: Known as the PMO, this team works with engineering, sales, customer service and finance, among other teams, to ensure that Groupon’s large-scale initiatives are efficiently executed. In particular, they are the liaisons between technical and non-technical functions.

“We’re the air traffic controllers of the engineering department, guiding projects home safely and being proactive about preventing any issues,” said Hyatt.

IMPACT: Because these are high-stakes projects, the team affects the entire business.

TEAM INCLUDES: A college hire and one-time Groupon intern, and others with both technical and non-technical backgrounds.

SUGAR HIGH: This team has a sweet tooth, celebrating a project’s completion with cannoli cake and a team member’s marriage with a rainbow cake.

IDEAL CANDIDATE: Anyone with an innate bias for action and strong technical command, plus the lust for learning required to work with multiple product and engineering teams.

You work with teams from varied departments and disciplines. Do you ever encounter disagreements about how to execute?

Hyatt: If you’re doing something worthwhile, with people who care, almost everyone will have an opinion about how it should be implemented, which is bound to result in a disagreement or two.

I approach those situations by getting everyone in the same room and facing it head on. But first, I take a step back to remind everyone that we all ultimately want the same thing: we want the product to launch and be successful.

Does PMO have a reputation in the company?

Hyatt: I’m proud to say it does. We’ve garnered the reputation of being vital to the success of any large-scale project. Because of that, our services are in high demand.

Reflect back on when you took this job. Is there anything about it that surprised you?

Hyatt: I was shocked by just how much I would get to learn. I come from a non-technical background. As I found my way into this role, I was worried that I wouldn’t have the technical knowledge base needed. Thankfully, having deep knowledge about a specific engineering area wasn’t necessary.

I’ve been able to build out my engineering knowledge because I’ve worked on such a variety of projects, including heavily consumer-facing projects, projects that are more focused on infrastructure — and everything in between. I get to learn something new about technology all the time, which I absolutely love.

JUAN GARCÍA, CHICAGO PMO LEAD
García spends much of his time facilitating other teams: coordinating meetings, optimizing processes, communicating and making sure stakeholders are accountable. As the team lead, he also ensures that his project managers have what they need to develop as professionals.

BEYOND WORK: García started running to get to know Chicago’s neighborhoods.

Has your team had an effect on the rest of the organization?

García: During the past three to four years, our project managers have helped teams deliver initiatives more efficiently by narrowing communication gaps, optimizing processes and sharing our project management knowledge.

Describe your team culture.

García: We truly care for each other, whether by covering for someone who needs time off, celebrating successes or supporting someone during challenging times.

Personally, the team has shown how much they care about me and my family on multiple occasions. Once, they surprised me with a rainbow cake and a celebration the day after I married my lifelong partner.

Reflect back on when you took this job. Is there anything about it that surprised you?

García: My first impression was that I had freedom to propose changes and improve the way our team worked. Coming from a corporate environment, the difference was huge. Team members are empowered to propose solutions and bring them to reality.

Describe an ideal candidate for this team.

García: Someone who can adapt to change easily, has a bias for action, is driven to find solutions and get results and enjoys helping others.

ATTICUS BIKOS, TECHNICAL PROJECT/PROGRAM MANAGER
Bikos spends a good deal of time managing and mitigating risks. He resolves or escalates these by generating possible solutions, facilitating trade-off decisions, making recommendations on resolution and removing obstacles.

Every day is different. But generally, how does your day tend to break up?

Bikos: I try to allow myself time in the morning to ramp up by reading emails — with coffee. I maintain project documentation for my teams, so I spend a chunk of time making sure that is up to date. But much of my day is spent in meetings, mostly dealing with mitigating risks if they are identified, planning for what’s next, determining how can we move faster and discussing current project status.

How do you manage disagreements among various teams and disciplines?

Bikos: Disagreements are natural and healthy. But, after a certain point, we need to make a decision and act. I believe that much of the conflict goes away if everyone in the room agrees what’s most important and where we should dedicate resources and energy.

Reflect back on when you took this job. Is there anything about it that surprised you?

Bikos: I never thought I’d be in the same room with VPs, seasoned engineers and even the executive team. And I definitely never thought they’d be looking to me for critical information. I was a college grad hire — thrown into the deep end real quick. But with guidance and support, I made it through, and now I feel more confident than ever in my abilities.

ANDREW WHIPPLE, TECHNICAL PROJECT MANAGER
Whipple started as an intern. “If you told me back as a college junior that I’d be a point person for some pretty huge projects,” he said, “working hand-in-hand with senior tech leaders all across the company, under no circumstance would I have believed you!”

BEYOND WORK: He’s a podcast junkie.

In your opinion, why is a group like PMO necessary?

Whipple: Groupon has a lot of teams that do great work, but sometimes there needs to be that dedicated link among all the teams, making sure that everything gets done and everyone is working towards the same goals.

Share something you love about your job.

Whipple: I love figuring out how best to get technical ideas across, even if I don’t understand them the way an engineer would, to various audiences — and hopefully do it in a way that’s fun.

At this moment, what does your typical day look like?

Whipple: Currently, I’m almost entirely dedicated to one team with members across locations, from India to Romania to Palo Alto. Up to half my day is spent in meetings to keep everyone on the same page and collect the information we need. The rest of the time is emails, scheduling and documenting.

Describe a product launch you enjoyed being a part of.

Whipple: I just wrapped up a project with our IT and multimedia teams to replace our videoconferencing tools, and I’m thrilled to say the project went smoothly. But what really stands out is that the project involved testing the potential solution.

Running that trial was a great opportunity to bring some user research skills that I don’t usually apply in my normal work. The special projects are ones where I feel I can bring a unique perspective and skill set beyond the usual PM toolkit.

How does your team find people who will be a good fit?

Whipple: We don’t limit ourselves to looking at the resume. In fact, I spent most of my internship interview talking about how being a stage manager for a Shakespeare company was like project management. Apparently, that convinced someone!